Something to know about Southwest credits: Say you buy a ticket on Feb. 1 for $300. At some point, the fare drops to $275 so you rebook and have a $25 credit. That credit is good for one year from 2/1 (original purchase date). On Sept. 30th you buy a $200 ticket and apply that $25, but due to a work obligation that comes up, you find out in December that you have to cancel that trip. Because you applied the credit from 2/1/15 to that ticket, the ENTIRE $200 will now expire on 2/1/16. I learned this the hard way!

Bottom line, if you are using a credit toward a new ticket, book the new ticket as two one-way flights instead of a round-trip. That way if you are forced to cancel, only part of the total cost will expire early. Make sense?

I've got $75 that will expire in May so now I'm trying to find a cheap weekend trip so I don't lose it. It figures that my upcoming jamaica trip returns after my credit expires so I could only apply money toward the outbound flight. Hence, the remaining credit.